Vanillin → HCID 87757280, compound

HRID 899019Notes

Reaction equation

HRID 899019 reaction equation
Cl[CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[O:7]=[CH:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C.O>CN(C=O)C>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([CH:17]=[CH:16][C:14]=1[O:15][CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])[CH:8]=[O:7]

Participants

6

Reactant 4

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 75361Silane, (chloromethyl)trimethyl-HCID 19096565Water ethanol

Product 1

HCID 87757280HCID 87757280, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Chloromethyltrimethylsilane (36.7 g, 0.3 mol) is added dropwise over 10 minutes to a mixture of vanillin (45.6 g, 0.3 mol) and potassium carbonate (41.4 g, 0.3 mol) in 300 ml of dry DMF maintained at 100° C., and while sparging with nitrogen. The mixture is left at 100° C. for 2 hours. The reaction mixture is filtered and the solvent is removed from the filtrate by distillation under vacuum. The final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg. 70 g of a pink syrup, which crystallizes, are obtained. After recrystallization from an 80/20 ethanol/water mixture, 35.5 g (yield: 50%) of 3-methoxy-4-trimethylsilanylmethoxybenzaldehyde are obtained in the form of white crystals (m.p. 45° C.), which are used without purification in the next step.

Workup

  1. customwhile sparging with nitrogen
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent is removed from the filtrate by distillation under vacuum
  4. customThe final traces of DMF are removed via a stage at 60° C. under a vacuum of 2 mmHg
  5. custom70 g of a pink syrup, which crystallizes
  6. customare obtained

Sources & evidence

ORD record
ord-305c1502a46444dc85e00fb32f5b5349
Source dataset
uspto-grants-2008_04
Patent number
US07354571B2

Reaction notes

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